Treatment of tobacco smoke



Jan. 1.2, 1960 J. w. KINNAVY I 2,920,416 TREATMENT OE TOBACCO SMOKE Original Filed July 23, 1958 lez/gaar Toco nited States Patent O TREATMENT on roaAcco sMoKE lames W. Kinnavy, Chicago, Ill., assignor to Wallace A.

Erickson & Co., Chicago, Ill., a corporation 'of Illinois 16 Claims. (Cl. ISI-208) This invention relates to the treatment of tobacco smoke for the purpose of reducing the presence of undesired constituents therein and means to accomplish this result.

This application is a division of my Tobacco Smoke Filter application, Serial No. 750,524, lfiled July 23, 195-8, which, in turn, is a continuation-in-part of my application Serial No. 726,273, filed April 3, 1958.

The harmful physiological effects of volatile constituents contained in tobacco smoke have long been recognized. It is well known, for example, that tobacco smoke contains various alkaloids and health-affecting volatile'materials such as nicotine and also tarry and other constituents which tend to physiologically irritate the smoker. Attempts have been made to obviate the harmful effects induced or aggravated by these materials by using filters. However, the various filtering devices and processes of the prior art have not been entirely satisfactory, although in many cases they remove, to some degree, toxic materials. For example, some of the methods and devicesused for filtering tobacco smoke fail to satisfy completely the needs of the smoker or tobacco industry because they only remove a small portion of the toxic materials, are inconvenient to use, unfavorably influence the taste of the tobacco smoke, or adversely affect the burning characteristics of the tobacco.

I have found that it is possible, by use of a simple filtering operation and device, to remove substantial quantities of the harmful constituents of tobacco smoke evolved from burning tobacco. This is `accomplished Iby contacting tobacco smoke with quaternary ammonium compounds having the general formula:

wherein: R, R1, R2 and R3 are the same or different members of the group consisting of alkyl and aryl (includes nuclear substituted aryl groups) radicals; and

is the cationic moiety of said formula.

The nicotine and tars of tobacco, smoke become bound to the above-mentioned quaternary compounds. Although these quaternary ammonium compounds serve to retain alkaloids such as nicotine and tars present in .tobacco smoke without requiring the use of other filter materials or a porous carrier, these compounds may be retainedby materials which` serve as fa filter -as well as a carrier for the quaternary ammonium compounds. For example, the acetate compounds may be adsorbed Ion porous material such `as exemplified by cellulosic products (e.g., cellulose acetate, paper, cotton, and Wood), asbestos wool, particles of pumice stone, silica ICC porous or carrier materials may be formed in the shape of cylindrical cartridges or inserts, or packed in cylindrical capsules or envelopes. Whatever form or shape filter is used, it may be retained within smoking articles such as cigarettes, cigars, cigarette or cigar holders, or pipes in a conventional manner, thereby permitting tobacco smoke to be drawn into contact with the filter before entering the mouth of the smoker.

The invention is illustrated in the accompanying drawing which shows a partially broken away perspective view of a cigarette having disposed therein tobacco and a tobacco smoke filter adapted to permit the passage of smoke therethrough. The filter comprises a cylindrical insert of asbestos wool having the above-mentioned. quaternary ammonium compounds retained therein. Thedrawing shows the same cigarette wrapper circumscrib ing the tobacco and filter insert.

The following examples illustrate satisfactory pro-- cedures for distributing the quaternary ammonium om cotton Ifibers to form a Ifilter.

EXAMPLE I About 1390 parts by weight of about a 25% isopropyl valcohol solution of trimethyloctadecylammonium chloride may be added to a vessel containing about 2 grams of cotton. About 328 parts by weight of about a 25% mixture of sodium acetate solution in water should then be added at room temperatures, with agitation, to the vessel.

An immediate reaction occurs whereby the resulting trimethyloctadecylammonium acetate is formed directly on the cotton fibers. 'I'his reaction may be shownVv In this process, the trimethyloctadecylammonium chloride is first adsorbed by the cotton, and trimethyloctadecylammonium acetate is afterwards formed directly on the cotton fibers upon the addition of sodium acetate to the vessel.

The deposition of about one gram of trimethyloctadecylammonium acetate on 2 grams of cotton produces: an excellent filter, although satisfactory results may be: obtained with less than this amount.

The impregnated cotton should be removedvfrom they vessel, dried in a conventional manner and formed intoa cylindrical filter for use in a cigarette. The resulting filter will have the cationic, water-insoluble trimethyloctadecylammonium acetate -afiixed to its fibers. Nicotine and tars become readily bound to the acetate retained by the cotton carrier.

The concentration of the reactants in this example is: not critical because a high proportion of the trimethyloctadecylammonium acetate reaction product formed in the liquid media will be deposited on and/ or adsorbed by the carrier irrespective of its concentration in the solution. However, a sufiicient amount of acetate reac-I tion product should be formed so asto vassure the deposition or formation of an effective amount of the reaction product on the carrier. As illustrated in the above equation, one mole of trimethyloctadecylammonium gel, cork, glass, wool, earth and plastic materials. These chloride and one mole of sodium acetate react to form one mole of trimethyloctadecylammonumacetate. y

, By using an anionic carrier, the ionic attraction of the cationic acetate reaction product to the anionic` carrieri Will be sufhciently great so as to tend to assure thehdep osition of high levels of acetate reaction product on the carrier. Therefore, it is advantageous to add, first, the chloride to the carrier and then add sodium acetate to the vessel so that the resulting reaction product is formed directly on the carrier. On the other hand, if desired, trimetnyloctadecylammonium acetate may be tirst formed, then substantially dissolved in hot chloroform, and finally applied as a solution to the carrier.

EXAMPLE ll in order to determine the comparative levels of alkaloids, such as nicotine and tars, that are removed from tobacco smoke when the quarternary ammonium compounds are used in conjunction with a carrier mass such as cotton, Cotton carriers were treated with the above referred to three classes of quarternary ammonium compounds and the resulting treated Carriers were tested under normal smoking conditions. More specifically, the quaternary ammonium compounds shown in Table I,

infra, were applied to 3 grams of cotton by saturating the cotton with 0.01 molar quantities of the chloride and sodium acetate reactants. The impregnated cotton samples were dried in a vacuum desiccator and the weight of the add-on quaternary ammonium acetate compound retained by each sample was determined. Then 0.25 grams each of the treated cotton samples that contained about (L09-0.16 gram of ne ammonium cornpound were used as a lter hed for a burning cigarette. Each cigarette was mechanically smoked at a substantially constant burning rate, designed to simulate normal smoking conditions, over a six minute period.

The results of these tests are shown in Table I, 1oelow.

Table I Grams ot' l Milligrams of Ammonium Nicotine and Quaternary Ammonium Compound Compound Tars Filtered- Retained by Out by Gram of Treated Cotton Cotton Filter Filter h n None .i None 1 8 Trimethylootadee xmmfmium Acetate i. 0.13 114. Trimetliylianrylimunoniuui .1cctate. 0. 16 29 Dimethyldioctadeoylamnu iuui Acente 0. l2 49 Dimethylethylbenzylammonjuui Acet e 0.09 26 Tetramcthylammonium Acetate 0.13 l

The above tabulated results show that the quaternary ammonium acetate compounds that were treated materially increased the level of alkaloids retained by the (untreated) cotton.

The foregoing detailed description has been given for clearness of understanding only, and no unnecessary limitations should be understood therefrom, as modifications Will be obvious to those skilled in the art.

Iclaim:

l. A tobacco smoke lilter comprising a supporting mass adapted to aiord passage of tobacco smoke therethrough, said mass including a quaternary ammonium compound having the generic formula wherein R, R1, R2 and R3 are selected from the group consisting of alkyl and aryl radicals, and

is the cationic moiety of said compound.

2. The filter of claim l wherein the quaternary ammonium compound is trimethyloctadecylammonium 3. The iilter of claim 1 wherein the quaternary ammonium compound `is trimethyllaurylammonium acetate.

4. The filter of claim l wherein the quaternary ammonium compound is dimethyldioctadecylammonium acetate.

5. The filter of claim 1 wherein the quaternary ammonium compound is dimethylethylbenzylammonium acetate.

6. The filter of claim l wherein the quaternary ammonium compound is tetramethylammonium acetate.

7. An improved tobacco smoke filter comprising a cylindrical tobacco smoke filter having an effective amount of a quaternary ammonium compound as a filtering aid, said quaternary ammonium compound having the generic formula RII! [RNR31+ is the cationic moiety of said compound.

9. The method of treating tobacco smoke to reduce irritating constituents therein, which comprises contacting the smoke with a quaternary ammonium compound having the generic formula wherein R, R1, Rz and R3 are the same or different members of the group consisting of alkyl and aryl radicals, and

is the cationic moiety of said compound.

l0. The method of treating tobacco smoke to reduce irritating constituents therein, which comprises contacting the smoke with a quaternary ammonium compound which is retained by a carrier, said quaternary ammonium compound having the generic formula wherein R, R1, R2 and R3 are selected from the group consisting of alkyl and aryl radicals, and

n n-Rn R1 is the cationic moiety of said compound.

5 11. A tobacco smoking article having disposed therein tobacco and a tobacco smoke filter adapted to permit the passage of the smoke therethrough, said lter comprising a supporting mass which includes a quaternary ammonium compound, whereby irritating constituents in tobacco smoke are retained Iby said lter when smoke from the burning tobacco is drawn through said filter, said quaternary ammonium compound having the gen eric formula RI 0 H l Il (l: [R-NRl]+[oc- Hr R1 Il wherein R, R1, R2 and R3 are selected from the group consisting of alkyl and aryl radicals, and

i" [n N-Rlv 12. The tobacco smoking article of claim 1l wherein the quaternary ammonium compound is trimethy'loctadecylammonium acetate.

13. The tobacco smoking article of claim 11 wherein the quaternary ammonium compound is trimethyllaurylammonium acetate.

14. The tobacco smoking article of claim 11 wherein the quaternary ammonium compound is dimethyldioctadecylammonium acetate.

15. The tobacco smoking article of claim 11 wherein the quatemary ammonium compound is dimethylethylbenzyiammonium acetate.

16. The tobacco smoking article of claim 11 wherein the quaternary ammonium compound is tetramethylammonium acetate.

References Cited in the file of this patent UNITED STATES PATENTS Schul' Jan. l, 1952 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTIGN Patent No. 2,920,416 January l2, 1960 James Wg, Kinnevy It is hereby certified that error appears in the printed specification of' the' above numbered patent requiring correction and that the said Letters vPatent should read as corrected below.

Column 4, lines 36 and 37, and lines 52 and 53, for ,"are

the same or different members of the group", each occurrence, reed are selected from the group Signed and sealed this 29th day of November 1960.

(SEAL) Attest:

KARL H. AXLINE ROBERT C. WAT-SGN Attesting OHicer T Commissioner of Patents 

1. A TOBACCO SMOKE FILTER COMPRISING A SUPPORTING MASS ADAPTED TO AFFORD PASSAGE OF TOBACO SMOKE THERETHROUGH, SAID MASS INCLUDING A QUATERNARY AMMONIUM COMPOUND HAVING THE GENERIC FORMULA 